4 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winona | 1 | 3,821 | 4,466 | -3.27% | 283 | 13.52 | City |
| Duck Hill | 2 | 1,531 | 656 | 12.91% | 1,481 | 1.03 | Town |
| Kilmichael | 3 | 554 | 636 | -2.81% | 188 | 2.94 | Town |
| Stewart | 4 | 159 | 50 | 7.43% | 141 | 1.13 | CDP |
Winona is the largest city in Montgomery County, with a population of 3,821.
Stewart is the smallest city in Montgomery County.
There are 4 cities in Montgomery County, Mississippi.